Head of Design (North America/Europe - Remote)

📍 Job Overview

Job Title: Head of Design (North America/Europe - Remote)

Company: Hospitable

Location: Remote (Oregon, United States; North America/Europe Timezones)

Job Type: Full-Time

Category: Product Design / Design Leadership

Date Posted: August 06, 2026

Experience Level: 5-10 Years (Implied)

Remote Status: Fully Remote

🚀 Role Summary

• Lead the product design vision, strategy, and execution for Hospitable's platform, ensuring an intuitive and elegant user experience.

• Build, mentor, and elevate a lean, AI-leveraged product design team, setting high standards for quality and output.

• Drive end-to-end design ownership, from discovery and research through to shipped features, with a focus on demonstrable impact.

• Champion the development and maintenance of a cohesive design system, language, style guide, and component library.

• Foster strong, collaborative partnerships with Product and Engineering leadership to shape the product roadmap and strategic direction.

📝 Enhancement Note: The role explicitly states it's a "player-coach" position, indicating a strong emphasis on hands-on design work alongside leadership responsibilities. The target candidate is expected to set the bar with their own design contributions while also raising the skill level of the team. The "AI-leveraged" aspect suggests an expectation for the candidate to be proficient with or open to integrating AI tools into the design workflow for efficiency and enhanced output.

📈 Primary Responsibilities

• Define and champion the overall design vision and standard for the Hospitable product, ensuring alignment with long-term company strategy and market positioning.

• Lead the design of the entire platform, owning the quality bar and ensuring every interaction is intuitive, every screen is elegant, and every feature is a joy to use.

• Execute high-stakes design work hands-on, including user research, discovery, prototyping, visual design, and interaction design.

• Develop, own, and maintain the design language, style guide, and component library, ensuring consistency and coherence across the growing platform.

• Proactively identify and eliminate design inconsistencies to reduce complexity and maintain a high-quality user experience.

• Build and lead a deliberately lean, AI-leveraged design team, establishing operational processes and raising the standard of shipped work through direct feedback and high expectations.

• Collaborate as an equal partner with Product and Engineering leadership, influencing product decisions and contributing to strategic roadmap development.

• Utilize research, analytics, experimentation, and customer feedback to inform design decisions and quantify the impact of design initiatives.

📝 Enhancement Note: The responsibilities emphasize a blend of strategic vision setting, hands-on execution, team leadership, and cross-functional collaboration. The "player-coach" aspect is critical, meaning the candidate will be directly involved in design creation while also guiding others. The focus on "AI-leveraged" design implies an expectation to integrate modern tools for efficiency and innovation.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent practical experience and expertise in design principles is essential.

Experience: A minimum of 5-10 years of experience in product design, with a significant portion focused on leadership and driving design quality within a product-led SaaS company.

Required Skills:

• Proven experience setting and raising the quality bar for design at a product-led SaaS company within the last 5 years.

• Demonstrated ownership of end-to-end design direction, from discovery and research through to shipped features, with a track record of measuring and communicating impact.

• Strong hands-on design proficiency, with a commitment to staying actively involved in design craft rather than moving to pure management within the last 3 years.

• Expertise in user research methodologies, customer feedback analysis, and translating insights into actionable design decisions.

• Proficient in shaping product strategy and holding an equal standing with Product and Engineering leadership.

• High level of agency, ownership, and comfort operating effectively in a lean, remote, low-bureaucracy environment.

• Mastery of design tools, specifically Figma for design and Whimsical for mockups.

• Excellent communication and collaboration skills for effective cross-functional partnerships. Preferred Skills:

• Experience within the short-term rental, travel, hospitality, or proptech domains.

• Familiarity with modern AI tooling and its application in design workflows.

• Experience in building and scaling design teams.

• A deep understanding of design systems and their implementation.

📝 Enhancement Note: The experience requirements are implicitly derived from the "within the last 5 years" and "last 3 years" clauses, suggesting a need for recent and relevant leadership experience. The emphasis on "still hands-on" and "player-coach" strongly implies that candidates with purely management backgrounds might not be the ideal fit. Domain experience is a significant plus, indicating a preference for candidates who can quickly grasp the industry nuances.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase end-to-end design projects demonstrating ownership from discovery to shipped features, highlighting your role and impact.

• Include case studies that clearly articulate the problem, your design process, the solutions implemented, and the measurable business impact (e.g., conversion rates, user satisfaction, efficiency gains).

• Present examples of how you have set and maintained a high-quality design bar, including visual polish, interaction design, and user experience.

• Demonstrate experience in developing or contributing to design systems, style guides, or component libraries, showing how they were used to ensure consistency and efficiency.

• Illustrate your product thinking and ability to collaborate with Product and Engineering, perhaps through examples of influencing product strategy or roadmap decisions. Process Documentation:

• Provide examples of your research and briefing processes, detailing how you gather insights and translate them into design requirements.

• Showcase how you've used data, analytics, experimentation, and customer feedback to inform and validate design decisions.

• Detail your approach to managing design quality control and providing direct feedback to designers to raise their standards.

• Outline your experience in developing and implementing design systems, including the rationale behind component choices and maintenance strategies.

📝 Enhancement Note: The portfolio is critical for this role, serving as the primary means to assess hands-on design skills, strategic thinking, and leadership impact. Emphasis should be placed on quantifiable results and the candidate's direct contribution to business outcomes, rather than just deliverables. The "player-coach" nature means the portfolio should reflect both individual design excellence and the ability to elevate others.

💵 Compensation & Benefits

Salary Range: The total cash budget for this role is between USD $171,000.00 to $218,900.00 annually. US employee gross salary may range from $157,619.92 to $201,771.94, adjusted for seniority and cost of living.

Benefits:

• Equity: Restricted Stock Units (RSUs) with a current grant value of up to $119,400.00, offering long-term upside value in the company.

• Performance Share Units (PSUs): Eligible for up to an additional $671,637 per year, tied directly to achieving clearly defined business performance targets and measurable outcomes.

• Healthcare (US Employees): Comprehensive health insurance options, including EPO, PPO, and HSA.

• Retirement Plan (US Employees): 401(k) plan.

• Paid Time Off: 35 days of paid time off per year, with encouragement to use it, plus self-serve public holidays.

• Parental Leave: Generous parental leave policy.

• Mental Health Support: Complimentary access to therapists via a dedicated Slack channel.

• Peer Recognition: A platform for earning virtual coins through peer recognition, redeemable for gift cards, donations, or monetary rewards.

Working Hours: While not explicitly stated as fixed, the role is full-time, and the remote, trust-based environment suggests flexibility. Standard professional working hours (approximately 40 hours per week) are expected, with an emphasis on output and results over strict time tracking.

📝 Enhancement Note: The compensation structure is highly variable, with significant potential through RSUs and especially PSUs tied to performance. This indicates a strong focus on impact and alignment with company success. The salary range provided is a broad estimate and will be adjusted based on the candidate's seniority, location, and cost of living. The PSUs are a notable incentive for high-impact contributions.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, Software-as-a-Service (SaaS), Hospitality Technology (Proptech/Short-Term Rental Software). Hospitable operates within the rapidly evolving short-term rental market, providing tools to automate and streamline rental management for hosts.

Company Size: Hospitable is a growing company, described as having a "deliberately lean" design team, suggesting a mid-size organization that prioritizes efficiency and focused talent. The "remote-only, global" nature indicates a distributed workforce.

Founded: Hospitable was founded with a mission to build software that allows short-term rentals to rent themselves, focusing on product and user experience. The company emphasizes a trust-based, results-oriented culture.

Team Structure:

• The design team is described as "deliberately lean" and "AI-leveraged," indicating a small, highly skilled group.

• The Head of Design reports directly to the CEO, Pierre, signifying a high level of visibility and influence.

• Collaboration is expected to be cross-functional and integrated, with the Head of Design acting as an equal partner to Product and Engineering leadership. Methodology:

• Data-Informed Decisions: Design choices are driven by research, analytics, experimentation, and direct customer feedback.

• Agile & Lean Operations: The company operates with low bureaucracy, moving fast and embracing modern AI tooling for maximum leverage.

• Trust-Based Autonomy: Employees are trusted to manage their work and deliver results without constant supervision.

• Radical Transparency: The company fosters an open and honest communication environment.

Company Website: https://hsptb.com/

📝 Enhancement Note: Hospitable's culture is characterized by its remote-first, trust-based, and results-oriented approach. The emphasis on radical transparency, lean operations, and AI integration suggests a modern, forward-thinking tech environment. The "Applicant Handbook" is a key resource for understanding their specific culture and recruitment process.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior leadership position within the design function, equivalent to a Director or VP level in larger organizations, but with a strong "player-coach" emphasis. It is the first dedicated Head of Design, meaning the individual will be instrumental in defining the future of design at Hospitable.

Reporting Structure: The Head of Design reports directly to the CEO, Pierre. This high-level reporting line provides significant visibility and influence over company strategy and product direction.

Operations Impact: The Head of Design will have a direct and substantial impact on Hospitable's product-led growth strategy. By owning the design vision and quality, they will shape user acquisition, retention, and overall customer satisfaction, which are critical drivers of revenue and market share in the SaaS space. The ability to make design decisions that improve conversion rates and user experience is paramount.

Growth Opportunities:

• Leadership Development: Opportunity to build and scale a design team from the ground up, establishing its processes and culture.

• Strategic Influence: Direct involvement in shaping the company's product strategy and long-term vision, reporting to the CEO.

• Skill Enhancement: Deepen expertise in applying AI tools within design, refining player-coach methodologies, and specializing in the proptech/short-term rental domain.

• Equity & Performance Incentives: Significant potential for financial growth through stock options (RSUs) and performance-based awards (PSUs), directly linking personal success to company achievements.

📝 Enhancement Note: This is a foundational role with immense potential for impact and growth. The direct reporting to the CEO and the opportunity to build a team from scratch offer a unique career trajectory. The compensation structure, particularly the PSUs, underscores the expectation for significant, measurable contributions to the company's success.

🌐 Work Environment

Office Type: Hospitable is a fully remote-only company, meaning there is no central office. The work environment is entirely distributed.

Office Location(s): The role is open to candidates in North America and Europe timezones, with specific mention of the East Coast of the US. The company also hires internationally as contractors or employees in the United States, European Union, and Australia.

Workspace Context:

• Remote Collaboration: The workspace relies heavily on digital collaboration tools (e.g., Slack, Figma, Whimsical) for communication, design work, and team interaction.

• Low Bureaucracy: The environment is characterized by minimal red tape, allowing for faster decision-making and execution.

• Trust and Autonomy: Employees are trusted to manage their time and workload effectively from their remote locations.

• AI Integration: Expect to work with and leverage AI tools as part of the daily workflow to enhance productivity and design capabilities.

Work Schedule: As a full-time, remote role, the work schedule is expected to be flexible, accommodating different time zones within North America and Europe. While approximately 40 hours per week are standard, the focus is on output and results, allowing for a degree of autonomy in managing work hours. Regular collaboration with team members across various time zones will be necessary.

📝 Enhancement Note: The fully remote nature requires strong self-discipline, excellent asynchronous communication skills, and comfort with digital collaboration tools. The flexibility comes with the expectation of high productivity and results. Candidates comfortable with a low-bureaucracy, trust-based environment will thrive here.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Application & Portfolio Review: Submit your application along with a portfolio that clearly demonstrates your end-to-end design ownership, impact, and leadership capabilities. Applications that articulate a clear "why this role and this mission" will stand out.

• Screening Call: A discussion likely focused on your background, motivations, and initial alignment with the role and company culture.

• Design Challenge/Case Study Presentation: Expect to present a detailed case study from your portfolio or tackle a specific design problem relevant to Hospitable's product, showcasing your strategic thinking, problem-solving skills, and design execution.

• Team & Leadership Interviews: Interviews with the CEO and potentially other key leaders (Product, Engineering) to assess strategic thinking, collaboration style, and cultural fit.

• Final Evaluation: A comprehensive assessment of your design leadership, hands-on skills, strategic thinking, and potential to elevate the design function and team.

Portfolio Review Tips:

• Focus on Impact: Clearly quantify the business impact of your design work (e.g., increased conversion rates, improved user satisfaction scores, reduced support tickets).

• Showcase Process: Detail your research methods, design thinking, and how you navigated challenges to arrive at your solutions. Use visuals to illustrate your process.

• Highlight Player-Coach Experience: Include examples of both your individual design contributions and how you've mentored, provided feedback, or raised the bar for other designers.

• Tailor to Hospitable: Emphasize projects that demonstrate experience in SaaS, product-led growth, or ideally, the proptech/hospitality domain. Articulate why you are passionate about Hospitable's mission.

• Demonstrate Tool Proficiency: Briefly mention your proficiency with Figma and Whimsical, and any experience with AI design tools.

Challenge Preparation:

• Understand the Domain: Research the short-term rental market, common pain points for hosts, and existing PMS (Property Management System) software.

• Prepare a Strategic Framework: Be ready to discuss how you would approach setting a design vision, building a design system, and leading a lean team in a remote, AI-leveraged environment.

• Anticipate Problem-Solving Questions: Prepare to walk through how you would tackle a specific design challenge, such as improving user onboarding, simplifying a complex booking flow, or enhancing reporting features.

• Articulate Leadership Philosophy: Be ready to discuss your approach to mentoring, giving feedback, and fostering a high-performance design culture.

📝 Enhancement Note: The application process emphasizes genuine interest and a strong portfolio that showcases both individual design excellence and leadership capabilities. The "player-coach" aspect means candidates should be prepared to demonstrate both their design skills and their ability to mentor and elevate others. The emphasis on "why this role and this mission" suggests personalized applications are highly valued.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core design tool for creating mockups, prototypes, and final visual designs. Proficiency is essential.

• Whimsical: Used for mockups, wireframing, and potentially flow charting. A key tool for rapid ideation and early-stage design.

• AI Design Tools: The role mentions "AI-leveraged design," indicating an expectation to utilize various AI tools for tasks such as idea generation, content creation, design iteration, or workflow automation. Specific tools may vary but adaptability to new AI technologies is key.

Analytics & Reporting:

• Product Analytics Platforms: While not explicitly named, proficiency with tools like Amplitude, Mixpanel, or similar platforms is likely expected to inform design decisions through user behavior analysis.

• Experimentation Tools: Experience with A/B testing platforms (e.g., Optimizely, VWO) to validate design changes and measure their impact.

• Customer Feedback Tools: Familiarity with tools for collecting and analyzing user feedback (e.g., surveys, in-app feedback widgets, user interview platforms).

CRM & Automation:

• CRM Systems: Understanding of CRM principles is beneficial, as design impacts user journeys within sales and customer success processes. Specific CRM tool knowledge (e.g., HubSpot, Salesforce) is a plus but not explicitly required for this design role.

• Project Management Tools: Experience with tools like Asana, Jira, or Trello for managing design tasks, workflows, and team collaboration.

📝 Enhancement Note: The core design stack includes Figma and Whimsical. The "AI-leveraged" aspect is a significant differentiator, suggesting that candidates who are already exploring or proficient with AI in design will have an advantage. While direct CRM/automation tool expertise isn't the primary focus, understanding how design impacts these areas is valuable.

👥 Team Culture & Values

Operations Values:

• Results and Output Focused: A strong emphasis on achieving measurable outcomes and delivering high-quality work rather than just putting in hours.

• Trust and Autonomy: Employees are trusted to manage their own work, time, and responsibilities, fostering a sense of ownership and empowerment.

• Radical Transparency: Open and honest communication is encouraged across all levels of the organization, leading to better decision-making and stronger team cohesion.

• Caring and Supportive: Despite a focus on results, the team environment is described as caring, suggesting a supportive culture where team members look out for each other.

• Efficiency and Leverage: A commitment to working smart, minimizing bureaucracy, and maximizing impact through lean processes and modern tools like AI.

Collaboration Style:

• Cross-Functional Integration: The Head of Design is expected to be an equal partner with Product and Engineering, indicating a highly collaborative and integrated approach to product development.

• Direct Feedback Culture: High expectations are set, and direct feedback is a key mechanism for raising the standard of work and fostering individual growth.

• Remote Collaboration Best Practices: Effective use of digital tools and asynchronous communication to maintain strong working relationships and project momentum across distributed teams.

• Lean and Agile Operations: A preference for streamlined processes, quick decision-making, and iterative development cycles.

📝 Enhancement Note: Hospitable's culture values autonomy, results, and transparency. The "player-coach" and "AI-leveraged" aspects suggest a forward-thinking, hands-on team that embraces efficiency and innovation. The emphasis on direct feedback and a caring environment points to a culture that balances high performance with personal well-being.

⚡ Challenges & Growth Opportunities

Challenges:

• Establishing Design Standards: As the first Head of Design, a key challenge will be defining and embedding design quality, consistency, and best practices across the organization.

• Building a Lean, Effective Team: Recruiting, mentoring, and maximizing the output of a small, AI-leveraged design team in a remote setting requires strong leadership and strategic talent management.

• Balancing Player and Coach Roles: Effectively managing time between hands-on design work and team leadership responsibilities can be demanding.

• Navigating Rapid Growth: Keeping pace with a fast-moving product roadmap and scaling design processes to support company growth without introducing excessive bureaucracy.

• Domain Specificity: Quickly gaining deep expertise in the short-term rental, hospitality, or proptech industry to inform strategic design decisions.

Learning & Development Opportunities:

• Design Leadership: Opportunity to build and shape a design function from its inception, defining its processes, culture, and strategic impact.

• AI in Design: Deepen expertise in integrating AI tools and methodologies to enhance design workflows and outcomes.

• Product Strategy: Gain significant experience influencing product strategy at a senior level, reporting directly to the CEO.

• Equity and Performance Incentives: Substantial opportunities for financial growth through equity and performance-based awards tied to company success.

• Industry Expertise: Develop specialized knowledge in the proptech and short-term rental market.

📝 Enhancement Note: The challenges are significant but directly tied to the growth opportunities. Success in this role will involve navigating ambiguity, establishing foundational processes, and driving tangible business results through design. The learning curve, particularly regarding domain expertise and AI integration, will be steep but rewarding.

💡 Interview Preparation

Strategy Questions:

• "How would you establish the initial design vision and quality bar for Hospitable, given our product-led SaaS model and remote structure?" (Focus on your process for setting standards, involving stakeholders, and initial steps.)

• "Describe your approach to building and leading a 'deliberately lean, AI-leveraged' design team. What are your key strategies for raising the standard of work and ensuring high output?" (Highlight your player-coach philosophy, feedback mechanisms, and integration of AI.)

• "Walk us through a time you shaped a product strategy or significant feature through your design thinking and collaboration with Product and Engineering leadership." (Provide a concrete example demonstrating your strategic influence and cross-functional partnership.)

• "How do you balance hands-on design work with leadership responsibilities? Provide an example of a high-stakes design project you led yourself recently." (Showcase your ability to execute and delegate effectively.) Company & Culture Questions:

• "Why are you specifically interested in Hospitable and our mission to automate short-term rentals, rather than other SaaS companies?" (Demonstrate genuine interest and research into the company and its market.)

• "How do you see yourself contributing to our radically transparent and trust-based remote culture?" (Align your working style with Hospitable's values.)

• "Describe your experience working in a low-bureaucracy, high-autonomy environment. How do you ensure accountability and results?" (Highlight your self-management skills and focus on impact.) Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly articulate the problem, your role and process, the solution, and the measurable impact. Use a storytelling approach.

• Quantify Impact: Emphasize metrics and data that demonstrate the success of your designs (e.g., conversion rate increases, user engagement improvements, efficiency gains).

• Showcase Player-Coach Skills: Be prepared to discuss both your individual design contributions and how you've mentored or influenced other designers.

• Highlight Tool Proficiency: Briefly touch upon your experience with Figma, Whimsical, and any AI design tools you've utilized.

• Connect to Hospitable: Explicitly explain how your experience and approach align with Hospitable's needs and mission.

📝 Enhancement Note: Interview preparation should focus on demonstrating both strong design craft and effective leadership. Be ready to provide specific examples that illustrate your ability to drive impact, collaborate strategically, and operate within a lean, remote, and AI-integrated environment. The "player-coach" aspect is crucial to address in your responses and portfolio examples.

📌 Application Steps

To apply for this Head of Design position:

• Submit your application through the provided link on Workable.

• Tailor Your Portfolio: Customize your portfolio to prominently feature end-to-end design projects that showcase your ability to set quality bars, drive impact through data, and lead design efforts. Emphasize your "player-coach" experience and any work with AI design tools.

• Craft a Compelling Cover Letter: Clearly articulate why you are passionate about Hospitable's mission and this specific role. Address how your experience aligns with the "player-coach" requirement and your vision for design at the company.

• Prepare for Case Study Presentation: Select 1-2 strong case studies from your portfolio to present, focusing on quantifiable results, your strategic thinking, and your leadership approach.

• Research Hospitable's Product: Familiarize yourself with Hospitable's current product offerings, target audience, and the competitive landscape in the short-term rental software market. Understand their existing design aesthetic and user experience.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.